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Search results; 219 places in Winchester

Guest favourite
Cabin in Colebrook
Adorable, storybook log cabin
6 beds
21–26 Apr
4.94 out of 5 average rating, 196 reviews
Guest favourite
Home in New Hartford
Mountain Serenity Lake View Pool & Hot Tub
5 beds
21–26 Apr
4.9 out of 5 average rating, 10 reviews
Guest favourite
Cottage in Litchfield
Litchfield - Hot Tub - Mohawk Mountain - Fireplace
3 beds
4–9 May
4.89 out of 5 average rating, 254 reviews
Guest favourite
Cottage in Southwick
Lake Views from Hot Tub Kayaks Fire Pit Central AC
4 beds
27 Apr – 2 May
4.97 out of 5 average rating, 63 reviews
Guest favourite
Home in Goshen
Charming renovated farmhouse with hot-tub
5 beds
18–23 Apr
4.9 out of 5 average rating, 48 reviews
Guest favourite
Guest suite in Granby
Onomea Farm
3 beds
23–28 Apr
4.97 out of 5 average rating, 60 reviews
Superhost
Cottage in Kent
NEW - Hot Tub - Mohawk Mtn - Appalachian Trl
3 beds
21–26 Apr
4.88 out of 5 average rating, 149 reviews
Guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
3 beds
25–30 Apr
4.99 out of 5 average rating, 201 reviews
Home in Morris
Luxury Compound, Pool, Hot Tub and much more.
7 beds
1–6 May
New place to stay
Guest favourite
Cottage in Burlington
Cozy Cottage w/Lakefront Views, Swim Spa & Firepit
4 beds
30 Apr – 5 May
5.0 out of 5 average rating, 40 reviews
Guest favourite
Home in Cornwall
The Owl Cottage@Mohawk Mountain
3 beds
26 Apr – 1 May
4.98 out of 5 average rating, 48 reviews
Guest favourite
Guest house in Cornwall
Charming Guest Cottage with Private Pool
1 bed
8–13 May
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Bethlehem
Lakeview Expanse
4 beds
4–9 May
5.0 out of 5 average rating, 15 reviews
Guest favourite
Cabin in New Hartford
Serenity Woods
8 beds
22–27 Apr
4.95 out of 5 average rating, 20 reviews
Guest favourite
Home in New Marlborough
Berkshires Colonial Farmhouse
7 beds
19–24 Apr
4.95 out of 5 average rating, 21 reviews
Guest favourite
Cabin in New Milford
Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit
2 beds
19–24 May
4.99 out of 5 average rating, 91 reviews
Home in Monterey
Forget-Me-Not by AvantStay | Bold Lakefront Escape
8 beds
24–29 Apr
4.9 out of 5 average rating, 21 reviews
Guest favourite
Home in Great Barrington
Jaw dropping mountain & lake views
4 beds
5–10 May
4.96 out of 5 average rating, 212 reviews